Antineoplastic agents 389. New syntheses of the combretastatin A-4 prodrug

George Pettit, Monte R. Rhodes

Research output: Contribution to journalArticlepeer-review

111 Scopus citations


Combretastatin A-4 as the phosphate ester prodrug (3d) is a potent antineoplastic and antiangiogenesis substance and is in advanced preclinical development. For the purpose of improving the phosphorylation synthetic sequence from combretastatin A-4, new routes were investigated. The phosphorylation step was found to be considerably improved using in situ-generated dibenzyl chlorophosphite. Cleavage of the benzyl esters employing a trimethylchlorosilane/sodium iodide procedure, followed by treatment with sodium methoxide, led to the water-soluble prodrug (3d) in high yield.

Original languageEnglish (US)
Pages (from-to)183-191
Number of pages9
JournalAnti-Cancer Drug Design
Issue number3
StatePublished - Apr 1998


  • Antineoplastic agents
  • Combretastatin A-4 prodrug
  • Phosphate esters

ASJC Scopus subject areas

  • Biochemistry
  • Oncology
  • General Biochemistry, Genetics and Molecular Biology
  • Pharmacology
  • Drug Discovery
  • Organic Chemistry


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